Starter Steps to Hiring your First Assistant

“If you don’t have an assistant, you are one.”  – Raymond Aaron

Who should I hire first?

It’s a common question among new business owners.  And my coaching is pretty straightforward…

If you’re a new business owner, your first hire should always be an accountant.

After that, get a bookkeeper.

When you get those out of the way, I encourage you to hire a personal assistant.


The Wrong (and Right) Hiring Order

I’ve heard some corporate-background business consultants spout off advice they’ve probably read in a book somewhere:

That your first hire should be someone who can bring in money – like, say, a salesperson.

I don’t even sort of agree.

Consider two things here…

Firstly, the typical left-brain corporate advisor type rarely has been in the trenches as a solo business owner like you, who is working out of your house, trying to run a family, plan meals, make a carpool and every other task under the sun. (AND he’s a man, right?)

In theory, yes it would be great if you could outsource the money-making part of your business…but that brings us to our second thing to consider, which is…

…which is that if you started your business with just a great idea and your skillset, you’re probably not ready to outsource the selling part – which is probably still a very delicate part of your business. (Exception is made for artists, writers and musicians who hire good agents.) Hiring a salesperson or marketer usually isn’t hiring. It’s abdicating…most likely because you’re hoping it’ll all just go away and never bother you again.

The problem is that you need to get better at sales, you need a system for how you sell, you need to understand your voice and message in both marketing AND sales before you can outsource them well. So, give yourself time to master this stuff while your business grows.

In the meantime, get other items off your plate. What takes up the bulk of your time? What gets in the way?  What little nose-bleed tasks keep tugging at you?  And most importantly, what do you use as a procrastination excuse every single day?

Wait. Before you answer. Let me share my own ridiculous story. This way you’ll feel much better about yourself…

All the Ways You Procrastinate  (Or…My Stupid Toothbrush Story)

Long ago in a galaxy far, far away, I worked out of my home when I wasn’t on the road. I was a performing songwriter running my own record label, and I never had enough time. (And this was before Facebook.) There were always a million things to do, and I could never even find the time to do them.

And yet…

I managed to do the dishes and complete a total clean up of the whole entire kitchen pretty much every day I wasn’t on the road.

Then one day, I caught myself scrubbing the kitchen sink with…ready for it?  A toothbrush.  You know those times where you glance at the edge of the stainless steel where the faucet meets the sink and discover what could only be a black plague of death hiding in there?  Well, that’s what happened to me.

So, I did what any average obsessive distracted person would do who’s avoiding doing her work.

I grabbed an old toothbrush, bleached it and started in on the sink, scrubbing furiously to get rid of the offending substance.

That’s when I woke up.

I was literally drowning in to-do’s.  I had money to deposit, songs to write, a producer to call, dates to book, checks in the mail for CD orders. (Like I said, this was before Facebook!)  And there I was, toothbrush in hand, bent over the kitchen sink giving my whole spirit (and precious time) to something that really didn’t matter.

Which is precisely when I hired my first personal assistant.

I was nervous. After all, nobody I knew had a personal assistant!  But in only a few hours per week, she took on the kitchen, the laundry, and the grocery shopping. (And presumably, the black plague of death in my kitchen sink.) She later did my bank deposits and CD orders.

I showed her what to do, and I made myself use the time to do the work that would ultimately pay me way more than her hourly wage.

I haven’t looked back since.  I now have a personal assistant 30 hours a week.  She helped me create an Operations Manual for my home, pets, husband and life.  At first it was in a binder. Now it resides in Evernote.

The Pre-Evernote Operations Manual to my Life!

The Pre-Evernote Operations Manual to my Life!

It’s never easy to hire someone. It seems there’s always a one-woman-show in your head with the never-ending monologue about how you should just be able to do all of this stuff. Or that by the time you show someone else how to do it and blah blah blah –

So, let’s bring up the house lights, stop the drama, and get started removing stuff from your plate, so you can actually, you know, focus on your business…


Five steps to hiring a personal assistant

1 – Brain dump.

This part’s fun. Grab a piece of paper or open Evernote – and write down every single thing you do in a week. Everything. Personal and business. Let fly, my sister. And don’t leave anything out just because it makes you embarrassed, or you’ve been meaning to stop doing that. This is all about seeing clearly.

2 – Identify your biggest (or most subtle) time thieves.

Now, look at your list. Identify which items steal your time and energy that could easily and quickly be outsourced. This is often the “low-hanging fruit.” These tasks could take anywhere from 5 – 50 hours of your time each week.

3 – Create a master list.

Create a list – not just of the tasks that you can outsource – but also the time you will be adding to your week just by letting them go. This will train your brain to see that you can actually take this time to work. (Once I started paying someone to do these things, I was less prone to wasting that time because I challenged myself to generate the income I was paying!)

4 – Determine how many hours you could outsource for starters.

You don’t have to get it ALL off your plate. Start small. How many hours could you hand off? How much is worth investing so that you can begin training yourself to focus on building your business? Write it down, make a plan.

5 – Create an ad and post it.

Do not avoid writing the ad. Writing the ad will make you a better employer. Writing an ad will sell YOU on the idea, as well as the ideal employee.

Then post the ad on a site like Craigslist or   Or ask your network for any suggestions.

6 – Interview and audition.

Do a series of interviews. Do the first interview outside of your home. That way, you don’t invite strangers to your home. Do not just do one interview. Do several interviews and make the prospect audition for a week, doing set projects – like the laundry. Or the black plague on your sink. Sit down and get their input, how they liked the work, if they noticed that something could be done better. See if they think like a helper. You don’t want another diva in your house! You’ve got that role covered!


The 5 Top Fears and Challenges of Hiring a Personal Assistant

Of course you have concerns and mental challenges with this simple process. Let’s address them head on…

Fear #1 – “Like I could find someone to do my shitty personal tasks.”

For some people, it’s mighty embarrassing to think of offloading the stuff that you hate doing.

Enter The Litter Box Rule.

I created The Litter Box Rule when people wanted to know my secret for finding personal assistants who have stayed with me for so many years.

The answer is that I’m clear and honest from the start.

First, I’m honest with myself. I’m unafraid to get clear about the menial tasks that need to get off my plate so I have time to run my business and have a life.

Second, I’m honest with my prospects. I don’t sugar-coat the truth about my life. (ie, cleaning the house before the cleaning lady arrives.)

That means that the ads I post are like any good marketing. They’re relentlessly honest so that prospects can self-select. In other words, if they’re going to be scooping the cat box, then I tell them up front. In fact, here’s a screen shot from an actual craigslist ad I posted a few years ago:

The Litter Box Rule

The Litter Box Rule means that being relentlessly honest about the role in any job description will set you up for success. When we hide who we are and what we need, we serve exactly no one. Least of all ourselves.

Fear #2 – “But I’m really picky about how I like things done!”

When people tell me this, I often discover that they’re terrified of being “found out.” They’ll be labeled a control freak. Or worse…a bitch.

Why not just own it? You like things the way you like them. This is why you have your own business, right? You’re not a bitch. You just know how it should be done.

I’ve found that the people who work for me love it when I am clear up front and can share exactly what a task looks like when it’s done and done well.

As with the Litter Box Rule above, let prospects know in your ad copy that you are picky – but that you’ll provide clear training and feedback to help them succeed. (You can always throw in a sideways smiley face to indicate that you at least have a sense of humor. 😊)

Fear #3 – “But they’ll judge me for the way I run my life and house!”

Confession: I now have a team of nine people. As I’ve added to my team over the years, one of my biggest fears has been the fear of being seen. Every. Single. Day. Being seen in my ups, being seen in my downs, being seen in my Lululemons – whatever.   So I am intimate with this fear.

So guess what…they may judge you. But more likely, they won’t.

I have discovered that in my interview process, I can ask them questions like, “Tell me something about you that I just have to know.” And I will find out if someone is critical merely by how they answer.

Fear #4 – I don’t know if I can trust someone to do all of those tasks. What if they steal from me?

This is why you begin your relationship with your personal assistant with only a few hours a week, a few projects a week. Go slowly – and watch the person work.

Then, if tasks involving money are required, start by using cash. (Remember cash?) And let the role evolve.

As the position expands into more hours, you can activate credit cards from your bank that are not connected to your main account. That way, if the person suddenly goes batshit crazy one day, you won’t wake up to discover your accounts have been drained.

Fear #5 – “I just feel guilty for hiring someone to do this stuff. I mean, Who am I?”

Buried deep within the DNA of some of us is a well-developed addiction to struggle. When we aren’t struggling, we feel bad. If you’re not doing it all, then you’re not living up to some ridiculously high bar you’ve set for yourself.

Okay, so I’m not going to argue with this part of you. She is probably many years old, and will fight me tooth and nail for her right to feel guilty for not struggling.

So, let’s start by hiring someone for just a few hours a week. Challenge your struggle-addicted self to use that time to be genuinely productive and focused. See if it rebalances how you view the need to have someone helping you.

Lists of possible tasks a personal assistant could do for you…

Let’s close with a list of the kinds of tasks a personal assistant could do for you each and every week.

  • Chopping vegetables
  • Grocery shopping
  • Picking the kids up from school
  • Walking dogs
  • Filling the bird feeders
  • Scooping the cat box
  • Dropping off dry cleaning
  • Picking up dry cleaning
  • Hand-washing delicates
  • Unpacking your luggage after a trip
  • Vacation prep work
  • Light cleaning
  • Cleaning the dinner dishes from the night before
  • Emptying the dishwasher
  • Folding the laundry
  • Filling your gas
  • Oil changes
  • All car service items
  • Random errands you always do on weekends
  • Vacuuming
  • Post office runs
  • Bank runs
  • Creating an Ops Manual for your house

Some of these items are things you may not want to take off your plate. (Picking up your kids, for instance.) But notice which items make you think, “Wow! You mean, I don’t have to do that anymore?”

So tell me how this makes you feel. Why would you (or would you not) hire your own personal assistant?

  • Michelle Dawnn


    You’re speaking my language, Christine OR maybe you’re reading my mind. lol

    Either way, I’ve been wanting to hire an assistant for years now! Another task now on my list to accomplish for 2018!!

    Thank you for sharing! Your emails are paving the way towards my business goals!

  • MJ

    I’ve always wanted a personal assistant to deal with the papers, filing, bills, house cleaning, etc!!

  • Keyanna

    I didn’t realize a personal assistant could be given household tasks such as dishes & laundry. I always thought of a personal assistant as someone who handles most office type issues such as paperwork, filing, bank errands, mail, etc. This has opened my eyes to a whole new world! Once I can afford an assistant I will definitely refer to this email and use this list.

  • Patricia King

    Excellent value in your post. So many truths.. i really enjoyed reading it as it definatley hit home for me. I am on my way to make my list. Thank you

  • Cat B

    This is what I put as my goal for this month toward the end of last year when I was goal setting. Great timing! I would love to hear more about what types of things might be best thru a virtual assistant. I might just be thinking that everything has to be done in person since that’s how I’ve done things so far. 🙂
    Thank you again! I printed it out so I can look at it with fresh eyes in the morning. 🙂

  • Miriam Ansley

    I am just getting started in my business and am trying to work 1 full-time and 2 part-time jobs! I really think hiring a PA for just 2 hours 3 days a week would even provide a lot of needed time! I will need to generate money to pay them but that is the whole point!

    thanks Christine for always putting things in perspective. You are transparent and so down to earth that you always make sense to me!

    thank you


  • April G

    Talk about serendipity. Hiring an assistant is a goal for 2018. I was just thinking how much more I could get done and how much quicker I could get client jobs completed. And honestly beOmg an organizer sometimes you just need to people to move things or hang pictures or just knock projects out. I found you when I first started this business and your advice to price things in packages was game changing. No more hourly for me. Thank you. Thank you. Another goal is to make it to your seminars. You are a blessing. Thank you.

  • Maylin

    Hi Christine,

    Thank you so much for the e-mail and this blog! I love your e-mails I learn something new every time! I was wondering if you have a template for the Ops Manuals for the home, business etc? I love to start my own this week!
    I love the idea to hire a PA. I had a virtual one and it was helpful. I would like to try your way as well and see which one will fit my lifestyle more!

    Again, thank you and I am looking forward to hearing from you soon!

  • Katherine

    This has really made me think. It would help to get a personal assistant. I’ ve always just moved faster to get it done or let the dishes sit there for a while, which of course just feeds into anxiety. But now that I’m older it’s harder to move faster to get it all done and your right, we don’t have to do it all ourselves. Good article, but you missed preparing meals, on the list. That’s my biggest challenge since I have allergies and low blood sugar and have to eat frequently.


    Well said.


    I want an assistant.I need one.

  • Courtney

    What you can’t afford to pay an assistant but you desperately need one?

    • Courtney

      Sorry that is what IF you can’t afford to pay an assistant but you desperately need one?

  • Valerie

    Hey Christine! These are great tips! Thank you!

  • Sally Galloway

    I love your list of starter items for how a personal assistant could help me. My struggle addiction excuse looks like this, “I need to keep doing this all myself until I have (extra) money coming in from a paying client. Then I can invest in my [self, business, success, future…].” And then the Catch 22–“Because I’m so busy doing [whatever my toothbrush task is], I’m not clear on who my target market is and what I offer…” Maybe my first personal assistant will be a great sounding board to help me get clear on who my ideal client is!

  • Natasha

    This was right on time. I am actually doing an ad now for an assistant . But if I had any hesitation. This post/email is blowing the lid off of that so I can be sure to push send on that description today. Thank you

  • Sherrice

    Awesome information. I need a personal assistant in business myself. I live with my brother and was doing the house cleaning and all these issue’s came up. I am thankful. I need the business assistant and will hire a house cleaner to do my part here maybe we could split the help and pay her. How much again do you think a personal assistant would be worth? My daughter use to be my business assistant and could use the money just refuses to or did in the past.

    • Amy

      check craigslist for local price points and verbiage you like/don’t like for developing your own post.

  • Lena

    Great article! I actually have the same concerns with hiring my first “Business Assistant” so this will be helpful for that too. Can I ask, how much I should pay? My business is not making much right now but I think I could if I could get more organized. I could use help with bookkeeping, inventory, social media, etc.

    • Amy

      check out virtual assistant options on-line. Most of what you have listed can be done virtually by adding them to your online support services for easy maintenance and follow-up.

  • Lisa

    Thanks Christine –

    This post about the benefits of hiring a personal assistant was really helpful! I know I need help, but have the dynamic duo against me – after putting personal/family savings into my business, “how can I commit more funds to an assistant?” (Guilt trip anyone?) And “I’m supposed to be able to do it all, right?!” The listing of all I do in a day that you recommended was what helped me with the second challenge (Thank you so much!) And I also realized I have a comeback for the first issue too – I have three kids who are old enough to tackle many of the tasks that distract me at home. I can pay them, contributing to the family and teaching them good work ethic at the same time! Thanks for this exercise Christine – it was a great way for me to dig deeper into what was holding me back so I could move beyond it!

  • Christian

    Thanks for this great piece. I desperately want a PA in my life as a new business owner! Curious about whether I can expense this through my business though. You mentioned starting folks as contractors and then later hiring as employees. Do, or can, these types of tasks fall under your business?

    • Elaine Bailey

      Hi Christian, My understanding is that you can expense this through your business. I’d always recommend checking with your accountant.

  • Sarah

    I’m a single professional and I have trouble doing home tasks because I work during the day and can’t always make calls to deal with bills, insurance, parking tickets, travel, appts, etc. I don’t have a ton of extra money, but I really think I need to get some help managing these things to lower my stress. I have researched some of the prominent companies, and none seem to be exactly what I am looking for. I also hired cleaners to fold laundry and do dishes (plus other standard tasks), but that was challenging as well since most services wouldn’t fold laundry. Any suggestions for minimizing risk while being picky and quirky in my needs? Thanks!

  • Marla

    Wonderful article! I live in the Detroit metro area, would you have any suggestions on where to place an ad or any agencies to start with? I’m not comfortable placing an ad on Craigslist and I have not seen or heard of any companies in the area. Thank you!

    • Amy is national resource with local candidates. is another option if it’s available in Detroit. You could also check with local temp agencies or similar services. There usually services that cater to home care (housekeepers, personal assistants, house managers, estate managers, etc.).

  • Taylor Presley

    Christine, stumbled upon this article and LOVED!! We’re a high level personal assistant company in NYC ( and this article hit the nail on the head with everything from fears to having a PA to “where do I get started?!” Just wanted to say kudos and of course, if you ever need a GYST assistant (remotely if you’re not in NYC!), I’m an email away!

  • Moira Donohoe

    My husband is a vietnam vet with PTSD. He would never want strangers in our house, or even someone we know doing personal work. I would love to hire someone for some of these tasks, but it is a problem.

    • Cathy

      I’ll preface this by saying that I am also a vet with a hubby that has PTSD. I don’t know how bad your husband’s PTSD is or if he stays home 24/7. But, I’m sure he can be reasonable or reasoned with. Especially if it’s important to you. I think all husbands want to be able to provide love and comfort and are happiest when you’re happy also.
      I’m sure his home is where he feels the safest because there’s nothing unexpected going on while he’s there. (he can relax his need to control his responses) But, I doubt he’s there 24/7. If he has activities or things he does consistently away from the home that may be a time that is available for you to have a personal assistant to help with things around the house. As you get older it will become a necessity.
      There are some things you can probably delegate out that someone doesn’t have to be in your home to complete (or maybe he would be willing to do things at home to help you out more) like grocery shopping, food prep (meal prep), post office runs, etc. You could designate a time for them to come and make sure your husband is aware so he doesn’t get triggered.
      Talk to him with logic (it’s easier on a man’s brain to process) but get ready for emotional feedback. Ask questions that help him think thru it and let him come up with the solutions (some men really love this!!). If he says something about feelings make sure you respect it and ask questions “How can I help you with that” or “Is there a way that would be easier for you”, “What if we tried…”, etc. Try to see things from his perspective and triggers and see if he or you can think of a different approach that may work.
      Let him know you need help, you have too many things on your plate, you’ve found some things you’d like to delegate out for someone else to do to help lighten your load. You’d like his help sorting out which things he’d be okay with and how they can be handled to make life easy. You could show him your list and say “These first things I want/need to do/don’t feel comfortable delegating. These second things I would like to delegate and have someone take care of outside of the home. What do you think about that? These third things I would like to delegate but it would require someone to come into the home. I know you don’t want other people around too much because home is where you can relax. (or I want you to be able to fully relax at home so I don’t want other people around too much) What do you think about me having someone come over and helping me for an hour or two while you’re out _________? Then when you come home it’s just us and we can both relax because the work is done and we’ll both still have energy for what’s important to us.”
      Now, I realize some of this might not work for you depending on circumstances and everything but it’s a place to start. If he’s really emotionally adamant about not having anyone in the house then wait, let him calm back down to logical, and ask him what you’re going to do when you need the help and there’s no other choice. What if you or he breaks a hip, etc.
      Eventually we will all need outside help. How can we do it as easily and peacefully as possible?
      Hope this long note helps! 🙂

  • Jodi Fitzpatrick

    Another question: (Such a provocative article!). I have Power of Attorney for my dad and his “estate,” such as it is. This takes 2-3 hours per week but weighs on me like lead. If I delegate this and screw up, I’m in a very bad legal position. I guess I could pay myself, but that would be a huge issue for my dad, who expects everything free (after being abusive as hell–30 years of therapy and I’m still having to work hard to overcome it and be the person I want to be to serve in what I feel I’m here to do). As I write this, I see how fucked up this is and what I need to do. Thanks for the impetus and space to figure it out.

  • Jodi Fitzpatrick

    Another question: do you pay the assistant as a subcontractor or an employee? In CA, if they don’t have a biz license, you need to do payroll and taxes, thereby creating another job for yourself….

  • Jodi Fitzpatrick

    This is sort of weird. I’ve had a woman who cleans house and does laundry for several years ( and felt guilty about it, until August joined Uplevel Gold). So now I feel guilty that I haven’t needed to be prodded to do it! Invested in Amazon Prime that functions sort of like a shopping assistant; order sundries and they’re delivered in two days to the house. The article helped me see how much time I spend in the beloved dog. I once added up the hours; walking, chauffeuring to grooming and playgroup, feeding, brushing, medicating. It comes out to 12 hours per week; part time job, basically. Tho nothing near being a mom to human children! Lordy I’m not made of that tough stuff! I can see U can outsource the chauffeuring. It breaks of two work days and costs an hour round trip both ways. So I’d save 4 hours and have uninterrupted work time. Thank you, Christine! But huge guilt on this one. Biz in startup, never turned a profit, how can I justify, people will sneer, all the stuff that makes a good mindset challenge. Here we go….

  • Mickey

    Thanks for this post! My husband and I made the decision a few months ago that we are hiring someone to cook and clean when garden season begins (April). I’ve also recently been thinking about other tasks that I can delegate to her, as you’ve listed. It feels a little diva-ish, but we clearly haven’t been able to be our best selves and make our businesses as successful as they could be, so it feels like an excellent investment in our success and happiness.

    • Christine Kane

      Anne! I think this TOTALLY applies to someone in your position who is on that professional ladder. Congrats to you for recognizing the value of your free time!

  • Anne

    Perfectly timed post! 🙂
    I just spent part of my holidays – the 2 days I was going to use for getting a massage, reading a book, walking with the dog – instead, getting my car inspected, taking the cat to the vet, buying new litter boxes (happy new year kitties!), grocery shopping, putting the Christmas decorations away, and reorganizing the hallway closet (?!). I have a salaried position, (and a not-very-serious business on the side), and this was not work-time I was giving up. But it still seems affordable to have someone help with tasks that take time away from allowing the ‘best me’ to emerge each week, including allowing time for my own personal priorities – health, relaxation, taking classes for fun etc. Thanks Christine!
    P.S. I probably would still have re-organized the hallway closet myself – that sucker is now wicked TIDY!

  • Leonore

    Christine, this is a fantastic article. It really makes hiring an assistant seem much more accessible than I thought. One question: How do you determine how much to pay your personal assistant? I live in another country than you do, so would need to adapt the amount to what is locally appropriate — very likely higher than in the US because salaries for low-to mid-income employees are generally higher where I live. But I would be extremely interested in both your process for making that remuneration decision, how much you actually pay them in dollars, and how you give them raises over time.

    • Christine Kane

      Hi Leonore – Well, I’m in a radically different situation now than I was when I started hiring personal assistants! So I pay much more than I did back then. But when I started, the position was 5 – 10 hours a week – and I offered the most I could offer – which, at the time, was about $1 above minimum wage. I attracted people who were very excited about the part time nature of the job. At first, I paid in cash because I didn’t want to deal with employer taxing, etc. (And it wasn’t many hours) But I quickly moved into a full employee contract. I give raises usually every 6 months or every year. It depends on where I started the person’s pay. I don’t have a “set in stone” process for that. But once I realize I can trust someone – and they are really rockin’ it for me, I don’t want them to want to leave – so I give them bonuses at christmas, plus a raise once per year. But be careful with that or you might end up giving raises out of guilt – or because you’ve set up expectations. Your clarity and rules are extremely important!

      • Christine Kane

        The first person i hired was also a nanny working for someone else – so I could pay her as a contractor. (Contractors have to have more than one person paying them for similar work. Otherwise, they are legally considered employees.) You can look for that kind of person. I quickly changed over to employee. And this is why the very first paragraph of the article says you want to make sure you have an accountant and a bookkeeper – they will take care of all of those unpleasant employee details for you Jodi! 🙂

        • Christine Kane

          when I am in situations like this, i always call myself to be the healthy person in the relationship and ask for what I need. (You can let those inner children running around freely in your head know that you’ve got this. they don’t need to be worried anymore.) Just because a pattern seems locked in place doesn’t mean it is. 🙂 I encourage you to get paid and break old patterns as often as possible.

  • Carolyn

    Wonderful article, Christine! I love the concrete suggestions, the guilt-free tone, the honesty. I’ve hired an assistant and yep, I still have to push through the fear that they’ll judge me. Thank you for normalizing!